


How Dean Got His Groove Back

by destielsfinest



Category: Supernatural
Genre: Angst, But still acknowledges that she's both, Cas has a shit ton of family, Cas prefers the her/she pronouns, Confused Dean, F/F, F/M, Fluff, Gender Confusion, Hermaphrodite Castiel, Inspired by a Movie, M/M, Mild Hurt/Comfort, Multi, Romance, Romantic Comedy, Sexual Content, Vacation
Language: English
Status: In-Progress
Published: 2016-02-05
Updated: 2016-02-05
Packaged: 2018-05-18 08:14:06
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,116
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5911690
Author URL: https://archiveofourown.org/users/destielsfinest/pseuds/destielsfinest
Summary: <blockquote class="userstuff">
              <p>Dean needs a vacation, so Sam gives him one. Together, with some friends, they tread through the beauty of Jamaica and get a taste of everything the land has to offer.</p>
            </blockquote>





	1. Metal Tube of Death

**Author's Note:**

> I'm new at this whole thing. But I love destiel, obviously lol, so I decided to try to write a fic about them. Also I'm looking for a beta so if want to help a girl out, message me. Much love (:
> 
> P.S. I know this one is kind of short, but it'll get longer once things start picking up (:

"Dean comes on. Why not? You _need_ this."

Sam, Dean's brother, said through the phone. Right now the giant that he claims relation to was trying to convince him to go on a trip to Jamaica. It wasn't that he couldn't afford it. Hell if Dean wanted to he could afford three trips to Jamaica, back to back. The issue was time — oh and the only way to get there is to _fly_.

"Because, Sam, they need me here. We're so close to sealing this deal, and they're hopeless without me."

Sam groaned, and Dean could practically see the bitch face that was _definitely_ on Sam's face.

"They don't need you there holding their hands. Don't you have someone that can handle things while you're gone? It's just a week Dean, but a week you desperately need. You've been busting your ass there for years now. Seven days without Dean Winchester isn't going to kill them."

Dean sighed, his resolve giving in a little. Sam was right. He hasn't really had time to himself since his promotion at Andover's. He was the Marketing Director. The main reason the company was racking in the money these days. Rubbing his hand against his forehead, he nodded.

"Alright. I'll think about it."

"Really?"

Dean could hear the smile on Sam's face.

"Yeah Sammy. I'll let you know tomorrow, alright?"

"Alright. Ok, and Dean?"

"Yea?"

"Don't call me Sammy."

And with that the little bitch hung up the phone. Rolling his eyes, Dean sat the phone back onto his holder. he walked to his refrigerator and grabbed himself a beer. Looking over at the pile of paperwork on his office desk, the blonde nodded his head, grabbing his phone.

"Hey Bela. I need a favor."

 

* * *

 

 

"Do you understand how important this is? We really need this deal. We all could get big bonuses."

"Yes Dean. I understand." Bela said through the speaker. "We nail this and all the boys get to walk around like they have big dicks. I get it." Dean rolled his eyes. "Are you ready? Your car will be there soon."

"I'm ready."

Dean being nervous was an understatement. In about an hour a metal tube was going to hurl him from New York to Jamaica. For 3 hours and 40 minutes Dean has to sit in a tiny seat, while a dude in a hat flies him 1,537 miles in the sky, 30,000 feet from the ground. Nervous didn't even begin to cover it.

"You're freaking out aren't you?"

"No."

"You're not a very good liar Dean. Take a couple of Xanax before boarding and you'll be fine."

"Will it kill me if I took them with whiskey?"

"If you want to be in a coma. Sure. Knock yourself right out."

"Thanks Bela. You always know how to be comforting."

"You're welcome Winchester. Have fun. Get laid. If not for yourself, at least for me."

Dean shook his head, a fond smile on his face. He heard the car pull up and he threw his jacket on, running a hand through his hair again.

"Goodbye Bela."

"Adios Dean."

They both hung up, and Dean was on his way to a tropical paradise, via a metal tubed death trap.

 

* * *

 

 

"Are you humming Metallica?"

Sam asked with too much calm and amusement in his voice.

"Shut up. it helps me calm down."

"It's amazing how everything in your life changed, except your _horrible_ taste in music."

"Listen, Nancy Grace, not everyone is calmed by ocean waves and whale noises."

Sam glared at him.

"At least I'm not scared of flying."

"It's a perfectly _normal_ phobia Samantha."

"Take your Xanax, drink your whiskey, and enjoy the flight. I heard there should be plenty of turbulence because of a rainstorm."

Dean visibly paled, gripping both armrests tightly. Sam smirked, putting in his headphones and leaning his head back against the seat.


	2. Blue Eyes

**Summary for the Chapter:**

> There's no Impalas in Jamaica, Sam brought reinforcements and something about horses.

Four hours later they are safe and sound on ground. Dean all but kisses the ground – because gross, that’s unsanitary.

“Land. Where we humans are _supposed_ to be.”

Sam laughs shaking his head.

“What traumatized you as a child that turns you into such a _pussy_ when it comes to flying?”

“The same thing that turns _you_ into a pussy when you see a clown."

Bitch face number 63 comes into effect.

“Clowns are killers.”

“So are planes.”

They made their way toward baggage claims, watching the bags pass as they waited for theirs.

“You do realize that there are more car crashes than plane crashes right?”

“Maybe so, but I rather crash in a car on the ground, than fall from the sky into unknown territory.”

Seeing his suitcase Dean grabs it and stalks towards the car rental place. He could only phantom the piece of crap car he’ll have to drive around because Impalas, as beautiful as they are, aren’t rentable. Sam clumsily follows him through the crowded airport, and Dean snorts. The boy was as graceful as a three – legged elephant.

Giving the brunette behind the desk a charming smile, he eyes her nametag.

“Charlene. I’m Dean Winchester. I believe I have a car waiting for me.”

Looking up she meets his smile with her own.

“Mr. Winchester,” She says with a heavy accent, typing his name into the computer registry. “Yes. There is a car for you.” Grabbing the phone to her left, she dials a number and waits for them to pick up. “Mr. Winchester is here to pick up his car. Thank you.” She hangs up and looks back at Dean. “They’re bringing it around for you, sir. Enjoy your stay in Jamaica.”

Dean winks at her.

“I surely will.”

He walks back over to Sam, whose messing around on his phone.

“Let’s go Samantha.”

“How long are you going to keep calling me that until it gets old?”

Dean pursed his lips, pretending to really consider the question.

“I’m 37 now, so thinking positively I’ll live until I’m about 84, so I have 47 years left to call you Samantha.”

The older Winchesters smirks, walking outside to the car that just pulled up. It was a black SUV, and Dean reframed from rolling his eyes. Why can’t people just have regular cars to rent?

“You call me Samantha, but you’re the one named after our grandmother, _Deanna_.”

“Yet you turned out to be the girly one.”

Sam huffed, and tossed his bag into the trunk. Dean followed suit, the smirk on his face permanent.

“It’s too bad that I couldn’t bring Baby. She would have loved to get some of this sun.”

“Would you like for me to order you a cassette player? I’m pretty sure they could get you one, ya know if time travel exist that is.”

“Shut it bitch.”

“Love you too jerk.”

Dean pulled out into the street.

“Where are we going?”

Sam pulled his phone out, going through his email to get the hotel name.

“The Hyatt. It’s about 20 minutes away from here. Just keep going straight.”

“So, nerd, what do you have planned for us?”

Sam raised an eyebrow.

“Uh, nothing? The point of a vacation is to do what you want. Let go. To _not_ follow a schedule.”

“Right. I know that. But, you know.”

“I don’t know.”

Sam eyed him for a second, before a grin spread across his face.

“What?”

“Did Dean, the infamous partier, forget how to have _fun_?”

Dean scoffed.

“What? No. I still know how to party.”

This was a lie. He hadn’t had time to party since graduating college. Adulthood came entirely too fast after that.

“Well good thing I brought in reinforcements.”

“What are you talking about?”

“You’ll see.”

 

* * *

 

 

“Well lookie here. You two finally decided to show up.”

Dean furrowed his eyebrows.

“Benny?”

“Long time no see Winchester.”

Dean smiled and pulled his friend into a one armed hug.

“Wow. How long has it been? 5 years?”

“Yes, 5 years too long. What have you been up to?”

“Working.”

“Sounds mighty fun, mate.”

Dean rolled his eyes.

“Please don’t tell me you’re here to pester me about my nonexistent social life too.”

“No, but I am here to help you get it back. Me and a few other people.”

“How many of you are here?”

That’s when Sam decided to walk over to them, after checking them in. Patting his hand on Dean’s back, he hands him his key.

“The whole gang is here.”

“The whole gang? As in who?”

“Brady, Gordon, Viktor, Charlie, Jo.”

“Jo? She’s our sister. Not a part of the gang.”

Sam shrugged his shoulders.

“Same difference.”

“Glad to know you love me so dearly Dean.”

The blonde turned around to see his little sister standing behind him. He stuttered a little, rubbing the back of his neck.

“You know what I mean Jo. You don’t want to be around us when we’re doing our man thing.”

“What is that exactly? All of you sitting around in a jerk it circle?”

Dean choked, holding a fist to his mouth as he coughs, Sam patting his back pretty hard.

“Jesus Christ Jo. What the fuck?”

The blond shrugged and started toward the elevator, a laughing Benny following her. Sam follows after them as Dean turns around to grab his suitcase. Turning back toward the elevators, his duffle bag swings along with the movement, successfully hitting someone and causing millions of papers to scatter around.

“Holy crap! I’m so sorry.” He immediately bends down to pick up the discarded papers. “I’m never this clumsy. That’s usually my brother’s forte.”

He hears a soft laugh before looking up and seeing a pair of blue eyes. A color blue he’s never seen before and he could have sworn he heard a gasp from the person before him.

“Uh, no. It’s, uhm, it’s totally fine.”

“Yea. Dean.”

Blue eyes furrow into a look of confusion.

“Huh?”

“My name. My name is Dean.”

He says, coming out of his trance. Blue eyes holds out a hand.

“Cas. That’s my name.”

Dean grabs Cas’s hand and shakes it, feeling smooth long fingers wraps around his hand.

“Nice to meet you.”

“Dean!” Sam yelled, holding the elevator door opened. “Come on. People are waiting.”

“Yea, Sasquatch, I’m coming.”

Dean’s eyes never look from Cas’ and Cas never looks away from him; but there’s a small smile appearing on her face. He hands that papers back gesturing his head toward his brother, sister, and friend.

“I should get going.”

“Yea.”

Cas’s smile becomes wider, and she shuffles the papers, stuffing them back into the manila folder they fell out of, all the while never averting her gaze. Behind him Dean hears a voice.

“Cassie! Come on! We’re going to be late.”

A look a pure irritation crosses Cas’ face and she finally looks from Dean and to the person that’s behind him. This gives Dean the perfect opportunity to check the rest of Cas out. She’s decked in a light blue blouse, with white denim shorts, and her feet were clad in white sandals; her toe nails matching the color of her shirt.

“Michael can hold his horses for two seconds!”

At her outburst Dean looks back up at her face, biting his lip to keep from laughing. Cas had fire, he liked that. Her gaze falling back on his, Cas graced him with another beautiful smile.

“Sorry. Family can be a little –“

“Overbearing? Yea I know. But you should go. It sounds kind of important.”

Cas lightly rolled her eyes. And for reason that draws Dean’s attention to the bangs that’s covering her forehead, and how he likes the way the ends of her hair curls. Most likely her hair responding to the humidity.

“Not really, but yea. I’ll see you later?”

Dean was a little shocked by the question, but he nodded.

“We’re at the same hotel. Pretty sure we’ll see each other around.”

Again he was met with a smile, this time it reaches her eyes and creates a cute little crinkle.

“Ok.” She nods. “See ya.”

She walks passes him and Dean follows her movements, watching as she walks towards a redhead. Once Cas reaches her, the other girl grabs Cas’ hand, looking toward Dean then back toward Cas and then they start walking away.

“Who is that?” He hears the redhead whisper.

“His name is Dean.”

“He’s cute.”

“I know.”

Dean smirks and turns to walk toward the elevator. Stepping in pass Sam, who is giving him the best bitch face he has, he leans against the elevator wall.

“Yeah Sammy. I think I’m going to like it here.”

The elevator door closes with Sam giving Dean a strange look, and Dean still smirking.

**Author's Note:**

> Leave comments and kudos. I want to know what you guys think. Until next time. Goodnight and goodbye.


End file.
